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Merck

O9890

5Z-7-Oxozeaenol

≥98% (HPLC), powder, TAK1 inhibitor

Synonym(s):

C 292, F 152, FR148083, L 783279, LL-Z1640-2

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About This Item

Empirical Formula (Hill Notation):
C19H22O7
CAS Number:
253863-19-3
Molecular Weight:
362.37
UNSPSC Code:
12352200
PubChem Substance ID:
329818946
NACRES:
NA.77
MDL number:
MFCD12912700

Key Documents

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Product Name

5Z-7-Oxozeaenol, ≥98% (HPLC)

SMILES string

COc1cc(O)c2C(=O)O[C@@H](C)CC=CC(=O)[C@@H](O)[C@@H](O)C\C=C\c2c1

InChI key

NEQZWEXWOFPKOT-BYRRXHGESA-N

InChI

1S/C19H22O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3-4,6-7,9-11,15,18,21-23H,5,8H2,1-2H3/b6-4+,7-3-/t11-,15-,18+/m0/s1

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

Quality Level

100

Related Categories

Application

5Z-7-Oxozeaenol has been used:
  • as transforming growth factor β-activated kinase 1 (TAK1) inhibitor to treat human colon cancer cells
  • as TAK1-specific inhibitor to provide intraperitoneal injection to mice for aortic banding
  • as TAK1 inhibitor to treat cells for luciferase reporter assay
  • to test growth and differentiation factor 2 (GDF2)-mediated anoikis

Biochem/physiol Actions

5Z-7-oxozeaenol is a potent ATP-competitive irreversible inhibitor of ERK2 (IC50 = 80 nM), TAK1 (MEKK7), MKK7, and MEK1, which all contain a common cysteine residue in the ATP-binding site. 5Z-7-oxozeaenol has no activity against other MAP kinases. 5Z-7-oxozeaenol is also anti-inflammatory.
The anti-inflammatory effects of 5Z-7-oxozeaenol may affect cardiac hypertrophy.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the MAPKKKs and MAPKs pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

O9890-1MG: + O9890-VAR: + O9890-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
0000497050
0000497050
0000354257
0000354257
0000229260

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Cytosolic Internalization of Anti-DNA Antibodies by Human Monocytes Induces Production of Pro-Inflammatory Cytokines Independently of the Tripartite Motif-Containing 21 (TRIM21)-Mediated Pathway
Park H, et al.
Frontiers in Immunology, 9 (2018)
Gang Wang et al.
Journal of cellular and molecular medicine, 25(14), 6584-6601 (2021-06-03)
Gastric cancer (GC) is the most frequent digestive system malignant tumour and the second most common cause of cancer death globally. Cancer stem cell (CSC) is a small percentage of cancer cells in solid tumours that have differentiation, self-renewal and
Epigenetic regulation of GDF2 suppresses anoikis in ovarian and breast epithelia
Varadaraj A, et al.
Neoplasia, 17(11), 826-838 (2015)
Te-Chia Wu et al.
Cancer research, 78(18), 5243-5258 (2018-07-18)
Inflammation affects tumor immune surveillance and resistance to therapy. Here, we show that production of IL1β in primary breast cancer tumors is linked with advanced disease and originates from tumor-infiltrating CD11c+ myeloid cells. IL1β production is triggered by cancer cell
Li Bo et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 84, 917-924 (2016-10-21)
Resistance to taxol represents a major obstacle for long-term remission in ovarian cancer. Transforming Growth Factor-β-Activated Kinase 1 (TAK1) is a critical component in immune response pathway. However, the role of TAK1 in the development of chemoresistance in ovarian cancer
View All Related Papers

Articles

MAPKKKs

The extracellular signal regulated kinase (ERK1 and ERK2) pathways are activated by mitogens and play an important role in controlling cell growth and differentiation.

Mitogen-activated Protein Kinases (MAPKs)

The mitogen-activated protein kinase (MAPK) family consists of stress-activated (SAPK) and MAPKs. Learn about their network of signal transduction cascades that mediate cellular responses to a diverse range of stimuli.

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